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The most notable feature of OKCupid is its matching system, which hinges on user answers to a large selection of wide-ranging questions, from politics and religion to bathing habits and hobbies. The answers to these questions serve to measure user compatibility, which OKCupid rates on a numerical scale. Using the question matching system, users can see their compatibility with other users and also their likelihood to be enemies. Users who answer enough questions can also submit their own questions to be used for matching.

When browsing other people’s profiles, users can see specifically where they match up or differ. The site compares answers across all users, so two people who are more literary or more adventurous than most other users can find each other more easily. The site’s quick match feature presents users with a sequence of strong matches, which they can either select or dismiss based on profile photos.

For paid users, OKCupid offers some extra features, including the ability to browse other user profiles invisibly and see a list of all the users who have ever "liked" their profile.